Acetic Anhydride → HCID 64498, compound

HRID 1424578Notes

Reaction equation

HRID 1424578 reaction equation
[NH2:1][CH:2]1[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1.CCOC(C)=O>[CH:9]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]([CH2:4]3)[CH:2]1[NH:1][C:12](=[O:14])[CH3:13])[CH2:8]2

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 253322-Aminoadamantane

Product 1

HCID 64498HCID 64498, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-aminoadamantane (20 g, 108 mmol) in dry pyridine (120 mL) was treated with acetic anhydride (12 mL, 128 mmol) and stirred overnight at rt. The mixture was dilute with EtOAc and washed with water, 1 N aq phosphoric acid and brine. The organic layer was dried, filtered and concentrated to give N-(2-adamantyl)acetamide (12.5 g, 60%). 1H NMR (400 MHz, CDCl3): δ=1.57 (m, 2H), 1.67 (m, 3H), 1.72 (m, 1H), 1.77 (m, 6H), 1.85 (m, 2H), 1.94 (s, 3H), 3.97 (t, 1H), 5.78 (br, 1H).

Workup

  1. washwashed with water, 1 N aq phosphoric acid and brine
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-281b11ab6ee248f6933c90729793ff7b
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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